Sweet Grass Fest

On the Saturday of Sweet Grass Fest the Big Timber Volunteer Fire Department opens the Fire Hall at 7 a.m. and serves a fundraiser breakfast. An hour and a half later runners check in at the City Hall parking lot for a 5K Fun Run put on by Montana on a Mission. Explore Big Sky places the course near the Boulder River. The fest is held over the last weekend of June. The Sweet Grass County Chamber of Commerce, which organizes it and takes its name from the county, calls it the county’s biggest event of the year. In 2026 it fell on Friday, June 26, and Saturday, June 27.

McLeod Street and 2nd Street on Saturday

By nine on Saturday morning McLeod and 2nd Streets are closed to traffic. Vendor booths line 2nd Street until four in the afternoon, with food trucks among them. A Kids’ Zone downtown has had a bouncy house, face painting and a petting zoo, according to a Lively Times listing. The Explore Big Sky calendar lists the street fair as free.

The car show runs on McLeod Street from 9 a.m. to 2 p.m. as a fundraiser for American Legion Post #19. Explore Big Sky describes it as a display of classic cars and tractors along Main Street. Once the cars clear, the parade comes down McLeod Street at 2 p.m. Entry is open to anyone who signs up. The theme for 2026 was “Independence and Freedom,” chosen for the nation’s 250th birthday.

The weekend also brings people home. High school classes hold their reunions during the fest. Christine Bakke, director of the Sweet Grass Chamber of Commerce, told the Big Timber Pioneer in 2023 that the reunions are always an enjoyable part of the weekend.

Two nights at the fairgrounds

The rodeo started the fest and still anchors it. The Visit Montana listing for 2025 opened with “Join Us Rodeo Weekend! Come celebrate our Rodeo heritage in Big Timber.” The B-T Rodeo Corporation runs it at the Sweet Grass County Fairgrounds, at 7 p.m. on Friday and 6 p.m. on Saturday. Explore Big Sky calls it NRA-sanctioned.

After the rodeo the music moves downtown. The Chamber’s schedule lists music downtown at 9 p.m. both nights, with the location and band announced later. On the opening day of the 2026 fest, the event’s Facebook page placed Friday’s concert in the Legion parking lot at 10 p.m., courtesy of VI Productions. Lively Times calls these evenings Rockin’ Rodeo after-parties in the American Legion parking lot. Explore Big Sky calls them street dances. One Lively Times listing, for a June 29–30 edition, named Kyle Park and Kimberly Dunn on Friday and the Robbie Walden Band with Tylor and the Train Robbers on Saturday. Tickets that year ran $15 to $20.

The rodeo’s hundredth year, in the rain

In 2023 Big Timber held the 100th year of its rodeo together with Sweet Grass Fest, and it drizzled through the weekend. The Pioneer counted about 450 people at the Friday rodeo. More than 1,600 came out for the Saturday performance in rain gear. There was no steady rain that Saturday, but it sprinkled on and off most of the day. Of the 52 vendors who had signed up, about half came.

“It was not as good of a turnout as years past due to the possibility of inclement weather,” Bakke said. The weather did not turn out as bad as forecast, and the parade and car show went ahead on Saturday. “The most cars they’ve had for a show is 106 and this year I think there were 40 or fifty,” Bakke said. “So still a good turnout.”

“The best part is that the weather held out,” she told the paper. “We really appreciate the community for coming out despite the possibility of bad weather. We tried to be as prepared for it as we could.” After that year, Bakke said, she officially had a “rain plan,” which she had not needed in earlier years.

Three years later the forecast was poor again. The 2026 schedule went out marked “rain or shine.” Vendor registration had passed the 2025 numbers more than two weeks before the fest. On June 30, 2026, the fest’s page thanked the 59 vendors “who braved the weather forecast.”